Seattle native Alex Calderwood has created the country’s hippest hotel chain in Portland, Palm Springs, New York City, and, of course, his hometown.

If you want to know where the cool kids hang out, follow Alex Calderwood. It’s not that he’ll lead you there. He’ll build it.

One September weekday, the Seattle native sat in his Ace Hotel New York, where a ballroom-size lobby offers the rarest of NYC treasures: free places to sit and free Wi-Fi. On stuffed wing chairs and dark velvet couches they perch, drink, read, converse. How do you know they’re the cool kids? It’s the hipster fedoras on their heads, the easy confidence as they sketch ideas for a start-up. Or measure them this way: To a one, every laptop in the lobby is an Apple.

Calderwood launched this hotel in a rare corner of Manhattan that hadn’t been labeled, celebrated, and emblazoned on a T-shirt. It’s three blocks north of Madison Square Park, among a mess of scuzzy cellphone shops and wig-and-perfume emporiums. It was the perfect raw space for a new venture, or what Calderwood calls his “art projects.”

Twenty years ago, Calderwood and his business partner Wade Weigel were the cool kids. Not that they’d describe themselves as such—Weigel just laughs and says they were “weird.”

Calderwood graduated Bellevue High and kind of meant to go to Seattle University, but somewhere between acceptance and matriculation he took one job, then another. Soon he was promoting club nights at Re-Bar and selling vintage clothing wholesale. Weigel threw his own parties in his International District underground club, the Lobby. The goal at every shindig was an eclectic mix: “Gay and straight, uptown and downtown,” says Calderwood. “We sort of collected people that were interesting.”

Armed with no business education and $16,000, they and a third partner, David Petersen, started Rudy’s Barbershop on Capitol Hill as a lark. The cheap haircuts by tattooed stylists were almost an afterthought; the real goal was another hangout, one where conversations carry down the line of vinyl chairs. Today the chain is 16 shops deep in four cities.

In 1996, the crew happened upon an empty flophouse in Belltown, a neighborhood then more overrun by homeless than hipsters. Some small rooms shared bathrooms—still do—but Calderwood embraced the rough edges. “What if we could make a hotel like someone’s Capitol Hill apartment?” mused Calderwood, who at 45 would still fit in on Pike/Pine, what with his wild black curls and jeans-and-blazer look.

That meant mod lines and reclaimed wood furniture. Beds are low to the ground. The clock radio is supplemented by a turntable and vintage records. Calderwood pictured his Capitol Hill archetype: “Maybe your friend is a street artist, so you have him paint something on your wall.” Shepard Fairey (now of Obama “Hope” fame) contributed some pieces; others are simply glossy magazine pages tacked to the wall.

Ace had its look.

Despite the homeless men that still slept on the stoop, Ace Seattle broke into the black in its first year. It catered to “what is now defined in the marketing world as ‘cultural creative’…looking back it’s obvious that it’s a quote-unquote market, but they were just people like us,” says Calderwood. The Ace name came from a card deck, where it plays both high and low—Ace Hotel sought the prince and the pauper.

The team tried again in 2007, this time transforming the decrepit Clyde Hotel in Portland’s West End. The double decker lobby meant room for a photo booth and seating to lounge, read, or argue the finer points of craft brewing. By 2009 Calderwood and team wondered whether the distinctly Northwest vibe would play in New York City. Fast-forward to the present at the 12-story New York Ace on 29th Street and Broadway. It’s saturated with Calderwood’s art-project style, with a two-story wall of graffiti and light fixtures made of glass meant for space telescopes.

Other than little lightbulbs that spell out “Hotel,” the building has no sign. But people find it anyway, filling the cavernous lobby. For a short time, small “Get a room!” signs tried to reserve spots for hotel guests, but they were pulled to cultivate a more welcoming ambience. Calderwood specifically hired security guards that eschewed the bouncer-on-steroids look. A relatively low price point, starting at $259 a night, helped.

“There’s always been a creative heartbeat between New York and the Northwest.”

Even though he eventually bought out his original partners, Calderwood is constantly pairing with others: the clothing company Opening Ceremony, celebrated chef April Bloomfield. He designed a Converse shoe. But his Northwest roots come first; mustached baristas man a Stumptown coffee shop in the lobby, and Pendleton blankets cover the beds upstairs. A Rudy’s outpost, the East Coast’s first, opened this summer.

New York, indeed, is enjoying a Northwest renaissance. Gotham has its own Beecher’s Cheese outpost and Glassybaby boutique, and Portland chefs making good at the Beagle and Pok Pok NY. Calderwood raves about (but claims he can’t afford) the angular wooden furniture by Oregonian Tyler Hays at BDDW in Soho. There’s no end in sight: A Nordstrom flagship should open in 2018. “There’s always been a creative heartbeat between New York and the Northwest,” Calderwood says of his Manhattan cultural cachet.

They say if you can make it there, you can make it anywhere. At about the same time Ace was opening in New York, Calderwood and company were busy smack-dab in the middle of anywhere: Palm Springs.

This is what life inside an Instagramphoto feels like. At the Ace in Palm Springs, the mid-September sunlight is pregolden, the buildings an evocative cream and orange without the benefit of a sepia filter. The San Jacinto Mountains are a dusty brown backdrop. The synthy ’60s sounds of “96 Tears” on the pool deck are just how a living Instagram pic should sound.

Here Calderwood goes native in the requisite T-shirt and bathing suit. The compound is repurposed from a 1965 Westward Ho Motel, later a Howard Johnson. “Retro” isn’t the half of it. In the King’s Highway eatery just off the lobby, site of an old Denny’s, the slate stone wall and line of rounded booths just beg to be the backdrop of a Rat Pack reunion, or maybe a talky Tarantino movie.

The hotel room walls are lined with tan canvas to resemble a kind of Bedouin tent, and the room-front carports are now personal patios, hidden behind cinderblocks and heavy wooden gates. But for all its private spaces, the clear centerpiece is, what else, one of Calderwood’s prized gathering spaces: the saltwater pool. In summer, the 104-degree hot tub is cooler than the baked concrete of the deck (and rooms are under $100), but eventually the desert falls into the frigid winter days—you know, in the upper 70s.

The pool deck is an Ace lobby, just warmer, and more a home base for the cruising class than the creative class. But peek at the books being read in front of the bikinis: Miranda July’s It Chooses You, Kurt Vonnegut’s Player Piano. The Jersey Shore it ain’t.

Palm Springs has 350 days of sun a year and its airport is even outdoors. Vacation starts before baggage claim.

Despite the see-and-be-on-the-scene vibe, Calderwood doesn’t think his hotels are just for hipsters (and no, he says he isn’t one either). It’s hard to imagine a family vacation during a party--heavy weekend or April’s raucous Coachella music festival, though weekdays are notably calmer.

You’re cool, too, say Ace Hotels. See, we left you an in-room vinyl copy of jazz guitarist Grant Green’s Idle Moments. The staff’s desire to eliminate elitism is frankly written across their chest on uniform T-shirts that read “P.S. I ♥ U.”

It’s not very hip—to say nothing of Northwesty—to wear affection on your sleeve so literally, but Calderwood really isn’t trying to be. Enduring, he says, and interesting, but not cool. He plans to open an Ace in Los Angeles next fall, and we hate to break it to him: It’s probably going to be cool.

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